MAGNESIUM SILICATE (synthetic) → 4-Carbomethoxy-3-(3-nitrophenyl)-7-(2-phenylethyl)-7-[(4-phenylphenoxy)methoxy]decan-5-one

HRID 1386840

反応式

HRID 1386840 の反応式
[C:1]([CH:5]([CH:18]([OH:47])[CH2:19][C:20]([CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)([O:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:29][CH:28]=1)[CH2:21][CH2:22][CH3:23])[CH:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)[CH2:7][CH3:8])([O:3][CH3:4])=[O:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C([O-])(=O)C.[Na+].[O-][Si]([O-])=O.[Mg+2]>C(Cl)Cl>[C:1]([CH:5]([C:18](=[O:47])[CH2:19][C:20]([CH2:39][CH2:40][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)([O:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[CH:29][CH:28]=1)[CH2:21][CH2:22][CH3:23])[CH:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)[CH2:7][CH3:8])([O:3][CH3:4])=[O:2]

参加物

6

反応物 4

HCID 61680MAGNESIUM SILICATE (synthetic)HCID 517045Sodium AcetateHCID 211831244-Carbomethoxy-3-(3-nitrophenyl)-7-(2-phenylethyl)-7-[(4-phenylphenoxy)methoxy]decan-5-olHCID 178418287HCID 178418287、化合物

生成物 1

HCID 211831254-Carbomethoxy-3-(3-nitrophenyl)-7-(2-phenylethyl)-7-[(4-phenylphenoxy)methoxy]decan-5-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of (3S),(7R) 4-carbomethoxy-3-(3-nitrophenyl)-7-(2-phenylethyl)-7-[(4-phenylphenoxy)methoxy]decan-5-ol (XIV, EXAMPLE 10, 11.12 g, 79.0 wt %, 13.73 mmol) in methylene chloride (530 ml) is added to a ground mixture of pyridinium chlorochromate (16.099 g, 74.685 mmol, 5.44 eq), sodium acetate (6.984 g, 85.14 mmol, 6.20 eq) and florisil (5.181 g) while maintaining less than 11°. The mixture is warmed to 21° and stirred at 20-25° for 20 hrs. The resultant slurry is filtered through magnesol (47.7 g) and rinsed with methylene chloride (375 ml). The filtrate is concentrated to an oil. An analytical sample of the title compound is obtained by chromatography (ethyl acetate/hexanes): TLC Rf=0.34 (ethyl acetate/hexanes, 10/90); HPLC rt=13.02, 13.23 min; NMR (CDCl3) 8.05-8.01, 7.60-7.00, 5.37, 5.21, 4.03, 3.94, 3.75, 3.58-3.43, 3.39, 2.96, 2.78-1.37, 1.20, 0.91, 0.71-0.61 δ; CMR (CDCl3) 200.89, 200.60, 168.29, 167.81, 157.10, 157.05, 148.38, 148.30, 143.58, 143.32, 141.99, 141.93, 140.73, 140.69, 135.29, 135.01, 134.78, 129.38, 129.23, 128.75, 128.45, 128.36, 128.23, 126.77, 125.91, 125.80, 122.96, 122.80, 122.04, 122.00, 116.16, 87.14, 86.92, 80.93, 80.44, 66.34, 65.92, 52.79, 52.35, 49.02, 48.62, 46.28, 46.20, 38.70, 38.51, 38.43, 37.99, 30.10, 29.52, 26.92, 26.71, 16.64, 16.39, 14.39, 14.16, 11.81, 11.58; MS (CI, ammonia) m/z (relative intensity) 656 (2.8), 655 (6.1), 136 (100).

後処理

  1. temperaturewhile maintaining less than 11°
  2. temperatureThe mixture is warmed to 21°
  3. filtrationThe resultant slurry is filtered through magnesol (47.7 g)
  4. washrinsed with methylene chloride (375 ml)
  5. concentrationThe filtrate is concentrated to an oil

出典と根拠

ORDレコード
ord-31b75d2ece6443528daad58aca640917
出典データセット
uspto-grants-2001_07
特許番号
US06265604B1

関連ノート

読み込み中…